The present invention features triazabutadiene molecules that provide adhesive functionality, e.g., triazabutadiene molecules as underwater adhesives or water-reactive adhesives. These triazabutadiene molecules mask an aryl diazonium ion, a highly reactive chemical functionality. Once unmasked, the diazonium species is adapted to react with an electron rich aryl ring that can undergo diazonium chemistry (e.g., phenol species, resorcinol species, etc.). Triazenes have previously been used to make an aryl diazonium species, but a strong acid was required (see Kimball, D. B. and Haley, M. M. (2002), Triazenes: A Versatile Tool in Organic Synthesis. Angew. Chem. Int. Ed., 41: 3338-3351). The use of strong acids may not necessarily be practical for particular applications. The triazabutadienes of the present invention can unmask the aryl diazonium species in water (or other conditions as described herein).
Inventors have surprisingly discovered that triazabutadienes can be used as additives in adhesive systems. For example, the present invention features triazabutadiene molecules that can be incorporated into epoxy adhesives. For example, a series of surprising orthogonal reactions featuring triazabutadienes and epoxy chemistry (as shown in FIG. 10A) provides for a new adhesive composition.